Manganese catalyzed cis-dihydroxylation of electron deficient alkenes with H(2)O(2)

• Published in: Organic & biomolecular chemistry Vol. 8; no. 19; p. 4444
• Main Authors: Saisaha, Pattama, Pijper, Dirk, van Summeren, Ruben P, Hoen, Rob, Smit, Christian, de Boer, Johannes W, Hage, Ronald, Alsters, Paul L, Feringa, Ben L, Browne, Wesley R
• Format: Journal Article
• Language: English
• Published: England 07-10-2010
• Subjects: Alkenes - chemistry; Catalysis; Electrons; Fumarates - chemistry; Hydrogen Peroxide - chemistry; Hydroxylation; Maleimides - chemistry; Manganese - chemistry; Stereoisomerism
• ISSN: 1477-0539
• DOI: 10.1039/c0ob00102c

A practical method for the multigram scale selective cis-dihydroxylation of electron deficient alkenes such as diethyl fumarate and N-alkyl and N-aryl-maleimides using H(2)O(2) is described. High turnovers (>1000) can be achieved with this efficient manganese based catalyst system, prepared in situ from a manganese salt, pyridine-2-carboxylic acid, a ketone and a base, under ambient conditions. Under optimized conditions, for diethyl fumarate at least 1000 turnovers could be achieved with only 1.5 equiv. of H(2)O(2) with d/l-diethyl tartrate (cis-diol product) as the sole product. For electron rich alkenes, such as cis-cyclooctene, this catalyst provides for efficient epoxidation.